Folks go to Door County—a bucolic peninsula between Green Bay and Lake Michigan—for the lakes, the art, and the cherries. I took my bride in search of something even sweeter.

The shores of Eagle Harbor, an inlet of Green Bay, have been attracting stone skippers of all ages for, well, ages.

(Anna Wolf)

Julie has a million happy memories of Door County. From the time we started dating, she would tell me stories about the blissful trips that she and her family made to the 70-mile-long peninsula in northeastern Wisconsin, the one whose endless shoreline and mellow charm have earned it the nickname "the Cape Cod of the Midwest." When I decided to propose, it didn't take long to figure out where to pop the question. In 2009, I finally got to see the place she had described with such affection, particularly the cabin on Kangaroo Lake that she and her sisters and her cousins used to visit every summer. We were married the following year.

But that trip to Door County was short, and left me regretting that I couldn't see more of the place that meant so much to her family, where they had made s'mores, gone swimming, and watched their beloved collie, Shelby, get skunked. After all, there's a funny paradox about where we vacation: The places we go to escape our daily routines can become, over time, a beacon of stability as the rest of our lives change. By the time I met Julie's parents, they'd moved away from the house in Kenosha where she'd grown up. Her childhood friends had scattered to Chicago and points east. But to hear her family tell it, Door County hadn't changed much at all. It sounded like the best-preserved remnant of Julie's younger days.

So on our next trip to the Midwest, I vowed to experience as much of Door County as I could: the sights, the sounds, and the tastes (especially the tastes). To pack the most experience into a short stay, we decided to make a loop of the peninsula, driving up one side and down the other. This wasn't an original approach: In 2010, the state's department of transportation had designated our route a Wisconsin Scenic Byway. But it left no doubt why so many families like Julie's keep coming back year after year, generation after generation.

The first mystery I hoped to solve was straightforward enough: What's with the cherries? Endless billboards trumpeting the glories of "Cherryland USA" had piqued my interest—as had the memory of delicious cherry pies that Julie's mom had baked over the years. So just north of Sturgeon Bay, amid weathered red barns and idling dairy cows, we pulled into Wood Orchard Market for a closer look (8112 State Hwy. 42, Egg Harbor, woodorchard.com, cherry jam $5). Julie had picked enough cherries in her day to take the place in stride, but to a novice from "back East" like me, the store inspired awe. Here, among other offerings, was the humble cherry in every form imaginable: dried and frozen; in strudel, soda, and cider; in both medium and hot salsa (better than you'd think!); and, of course, cartons of cherries au naturel, which we snacked on happily for the rest of the trip.

Julie isn't the first person in her family to make youthful memories of Door County. Her grandmother and three great-uncles bought their cabin in 1969, just in time to allow Julie's dad to spend his teenage summers here. To my surprise, he described the place back then as a kind of artists' colony. There are still far more galleries than you'd expect to find in such a bucolic scene. J.R. Jarosh, the co-owner of the Edgewood Orchard Galleries, a converted fruit barn that we passed a few miles ahead, told me that the galleries are here because of all the artists, and the artists are here because of the sublime raw material (4140 Peninsula Players Rd., Fish Creek, edgewoodorchard.com, handmade earrings from $15). "You think, sunrise and sunset—you have to go from Maine to Oregon to see both," he said. "But here it's two miles apart."

Julie and I almost immediately discovered what he meant: The little town of Ephraim hugs the shore of Eagle Harbor and offers an impossibly pretty view of beaches and little boats bobbing on the waves. But I was less interested in landscapes than in lunch. Before we left New York, Julie had set one culinary condition: no fish boils. These elaborate meals are all over the guidebooks, but her family avoids them: "Definitely a tourist thing," she said. In the heart of Ephraim, another tourist favorite proved too good to pass up. Wilson's, perched just across Route 42 from the water, was founded in 1906 and feels today like a '50s soda fountain or ice cream parlor (9990 Water St., Ephraim, wilsonsicecream.com, Chicago-style hot dog $5.50). To enjoy the full Midwestern experience, I ordered the tasty homemade root beer, and—a nod to the city that many of the peninsula's tourists call home—a Chicago hot dog. Julie advised me not to add my usual ketchup. "It's just not done," she said. "It doesn't add flavor." Which turned out to be true, as the dog arrived bearing most of the contents of a vegetable garden: peppers, onions, and more.

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